diff --git a/mcp_server/feature_mcp.py b/mcp_server/feature_mcp.py
index ce3859f..06535c7 100755
--- a/mcp_server/feature_mcp.py
+++ b/mcp_server/feature_mcp.py
@@ -984,5 +984,35 @@ def feature_set_dependencies(
         return json.dumps({"error": f"Failed to set dependencies: {str(e)}"})
 
 
+@mcp.tool()
+def ask_user(
+    questions: Annotated[list[dict], Field(description="List of questions to ask, each with question, header, options (list of {label, description}), and multiSelect (bool)")]
+) -> str:
+    """Ask the user structured questions with selectable options.
+
+    Use this when you need clarification or want to offer choices to the user.
+    Each question has a short header, the question text, and 2-4 clickable options.
+    The user's selections will be returned as your next message.
+
+    Args:
+        questions: List of questions, each with:
+            - question (str): The question to ask
+            - header (str): Short label (max 12 chars)
+            - options (list): Each with label (str) and description (str)
+            - multiSelect (bool): Allow multiple selections (default false)
+
+    Returns:
+        Acknowledgment that questions were presented to the user
+    """
+    # Validate input
+    for i, q in enumerate(questions):
+        if not all(key in q for key in ["question", "header", "options"]):
+            return json.dumps({"error": f"Question at index {i} missing required fields"})
+        if len(q["options"]) < 2 or len(q["options"]) > 4:
+            return json.dumps({"error": f"Question at index {i} must have 2-4 options"})
+
+    return "Questions presented to the user. Their response will arrive as your next message."
+
+
 if __name__ == "__main__":
     mcp.run()
diff --git a/server/routers/assistant_chat.py b/server/routers/assistant_chat.py
index 9209128..1c3ece5 100644
--- a/server/routers/assistant_chat.py
+++ b/server/routers/assistant_chat.py
@@ -207,12 +207,14 @@ async def assistant_chat_websocket(websocket: WebSocket, project_name: str):
     Client -> Server:
     - {"type": "start", "conversation_id": int | null} - Start/resume session
     - {"type": "message", "content": "..."} - Send user message
+    - {"type": "answer", "answers": {...}} - Answer to structured questions
     - {"type": "ping"} - Keep-alive ping
 
     Server -> Client:
     - {"type": "conversation_created", "conversation_id": int} - New conversation created
     - {"type": "text", "content": "..."} - Text chunk from Claude
     - {"type": "tool_call", "tool": "...", "input": {...}} - Tool being called
+    - {"type": "question", "questions": [...]} - Structured questions for user
     - {"type": "response_done"} - Response complete
     - {"type": "error", "content": "..."} - Error message
     - {"type": "pong"} - Keep-alive pong
@@ -303,6 +305,34 @@ async def assistant_chat_websocket(websocket: WebSocket, project_name: str):
                     async for chunk in session.send_message(user_content):
                         await websocket.send_json(chunk)
 
+                elif msg_type == "answer":
+                    # User answered a structured question
+                    if not session:
+                        session = get_session(project_name)
+                        if not session:
+                            await websocket.send_json({
+                                "type": "error",
+                                "content": "No active session. Send 'start' first."
+                            })
+                            continue
+
+                    # Format the answers as a natural response
+                    answers = message.get("answers", {})
+                    if isinstance(answers, dict):
+                        response_parts = []
+                        for question_idx, answer_value in answers.items():
+                            if isinstance(answer_value, list):
+                                response_parts.append(", ".join(answer_value))
+                            else:
+                                response_parts.append(str(answer_value))
+                        user_response = "; ".join(response_parts) if response_parts else "OK"
+                    else:
+                        user_response = str(answers)
+
+                    # Stream Claude's response
+                    async for chunk in session.send_message(user_response):
+                        await websocket.send_json(chunk)
+
                 else:
                     await websocket.send_json({
                         "type": "error",
diff --git a/server/services/assistant_chat_session.py b/server/services/assistant_chat_session.py
index 8c5c455..f030aa4 100755
--- a/server/services/assistant_chat_session.py
+++ b/server/services/assistant_chat_session.py
@@ -47,8 +47,13 @@ FEATURE_MANAGEMENT_TOOLS = [
     "mcp__features__feature_skip",
 ]
 
+# Interactive tools
+INTERACTIVE_TOOLS = [
+    "mcp__features__ask_user",
+]
+
 # Combined list for assistant
-ASSISTANT_FEATURE_TOOLS = READONLY_FEATURE_MCP_TOOLS + FEATURE_MANAGEMENT_TOOLS
+ASSISTANT_FEATURE_TOOLS = READONLY_FEATURE_MCP_TOOLS + FEATURE_MANAGEMENT_TOOLS + INTERACTIVE_TOOLS
 
 # Read-only built-in tools (no Write, Edit, Bash)
 READONLY_BUILTIN_TOOLS = [
@@ -123,6 +128,9 @@ If the user asks you to modify code, explain that you're a project assistant and
 - **feature_create_bulk**: Create multiple features at once
 - **feature_skip**: Move a feature to the end of the queue
 
+**Interactive:**
+- **ask_user**: Present structured multiple-choice questions to the user. Use this when you need to clarify requirements, offer design choices, or guide a decision. The user sees clickable option buttons and their selection is returned as your next message.
+
 ## Creating Features
 
 When a user asks to add a feature, use the `feature_create` or `feature_create_bulk` MCP tools directly:
@@ -402,6 +410,17 @@ class AssistantChatSession:
                     elif block_type == "ToolUseBlock" and hasattr(block, "name"):
                         tool_name = block.name
                         tool_input = getattr(block, "input", {})
+
+                        # Intercept ask_user tool calls -> yield as question message
+                        if tool_name == "mcp__features__ask_user":
+                            questions = tool_input.get("questions", [])
+                            if questions:
+                                yield {
+                                    "type": "question",
+                                    "questions": questions,
+                                }
+                                continue
+
                         yield {
                             "type": "tool_call",
                             "tool": tool_name,
diff --git a/ui/package-lock.json b/ui/package-lock.json
index 190768a..e54e47e 100644
--- a/ui/package-lock.json
+++ b/ui/package-lock.json
@@ -55,7 +55,7 @@
     },
     "..": {
       "name": "autoforge-ai",
-      "version": "0.1.6",
+      "version": "0.1.7",
       "license": "AGPL-3.0",
       "bin": {
         "autoforge": "bin/autoforge.js"
diff --git a/ui/src/components/AssistantChat.tsx b/ui/src/components/AssistantChat.tsx
index a9d8b5f..0592644 100644
--- a/ui/src/components/AssistantChat.tsx
+++ b/ui/src/components/AssistantChat.tsx
@@ -11,6 +11,7 @@ import { Send, Loader2, Wifi, WifiOff, Plus, History } from 'lucide-react'
 import { useAssistantChat } from '../hooks/useAssistantChat'
 import { ChatMessage as ChatMessageComponent } from './ChatMessage'
 import { ConversationHistory } from './ConversationHistory'
+import { QuestionOptions } from './QuestionOptions'
 import type { ChatMessage } from '../lib/types'
 import { isSubmitEnter } from '../lib/keyboard'
 import { Button } from '@/components/ui/button'
@@ -52,8 +53,10 @@ export function AssistantChat({
     isLoading,
     connectionStatus,
     conversationId: activeConversationId,
+    currentQuestions,
     start,
     sendMessage,
+    sendAnswer,
     clearMessages,
   } = useAssistantChat({
     projectName,
@@ -268,6 +271,16 @@ export function AssistantChat({
         </div>
       )}
 
+      {/* Structured questions from assistant */}
+      {currentQuestions && (
+        <div className="border-t border-border bg-background">
+          <QuestionOptions
+            questions={currentQuestions}
+            onSubmit={sendAnswer}
+          />
+        </div>
+      )}
+
       {/* Input area */}
       <div className="border-t border-border p-4 bg-card">
         <div className="flex gap-2">
@@ -277,13 +290,13 @@ export function AssistantChat({
             onChange={(e) => setInputValue(e.target.value)}
             onKeyDown={handleKeyDown}
             placeholder="Ask about the codebase..."
-            disabled={isLoading || isLoadingConversation || connectionStatus !== 'connected'}
+            disabled={isLoading || isLoadingConversation || connectionStatus !== 'connected' || !!currentQuestions}
             className="flex-1 resize-none min-h-[44px] max-h-[120px]"
             rows={1}
           />
           <Button
             onClick={handleSend}
-            disabled={!inputValue.trim() || isLoading || isLoadingConversation || connectionStatus !== 'connected'}
+            disabled={!inputValue.trim() || isLoading || isLoadingConversation || connectionStatus !== 'connected' || !!currentQuestions}
             title="Send message"
           >
             {isLoading ? (
@@ -294,7 +307,7 @@ export function AssistantChat({
           </Button>
         </div>
         <p className="text-xs text-muted-foreground mt-2">
-          Press Enter to send, Shift+Enter for new line
+          {currentQuestions ? 'Select an option above to continue' : 'Press Enter to send, Shift+Enter for new line'}
         </p>
       </div>
     </div>
diff --git a/ui/src/hooks/useAssistantChat.ts b/ui/src/hooks/useAssistantChat.ts
index b8fedff..cb660f6 100755
--- a/ui/src/hooks/useAssistantChat.ts
+++ b/ui/src/hooks/useAssistantChat.ts
@@ -3,7 +3,7 @@
  */
 
 import { useState, useCallback, useRef, useEffect } from "react";
-import type { ChatMessage, AssistantChatServerMessage } from "../lib/types";
+import type { ChatMessage, AssistantChatServerMessage, SpecQuestion } from "../lib/types";
 
 type ConnectionStatus = "disconnected" | "connecting" | "connected" | "error";
 
@@ -17,8 +17,10 @@ interface UseAssistantChatReturn {
   isLoading: boolean;
   connectionStatus: ConnectionStatus;
   conversationId: number | null;
+  currentQuestions: SpecQuestion[] | null;
   start: (conversationId?: number | null) => void;
   sendMessage: (content: string) => void;
+  sendAnswer: (answers: Record<string, string | string[]>) => void;
   disconnect: () => void;
   clearMessages: () => void;
 }
@@ -36,6 +38,7 @@ export function useAssistantChat({
   const [connectionStatus, setConnectionStatus] =
     useState<ConnectionStatus>("disconnected");
   const [conversationId, setConversationId] = useState<number | null>(null);
+  const [currentQuestions, setCurrentQuestions] = useState<SpecQuestion[] | null>(null);
 
   const wsRef = useRef<WebSocket | null>(null);
   const currentAssistantMessageRef = useRef<string | null>(null);
@@ -204,6 +207,25 @@ export function useAssistantChat({
             break;
           }
 
+          case "question": {
+            // Claude is asking structured questions via ask_user tool
+            setCurrentQuestions(data.questions);
+            setIsLoading(false);
+
+            // Attach questions to the last assistant message for display context
+            setMessages((prev) => {
+              const lastMessage = prev[prev.length - 1];
+              if (lastMessage?.role === "assistant" && lastMessage.isStreaming) {
+                return [
+                  ...prev.slice(0, -1),
+                  { ...lastMessage, isStreaming: false, questions: data.questions },
+                ];
+              }
+              return prev;
+            });
+            break;
+          }
+
           case "conversation_created": {
             setConversationId(data.conversation_id);
             break;
@@ -327,6 +349,49 @@ export function useAssistantChat({
     [onError],
   );
 
+  const sendAnswer = useCallback(
+    (answers: Record<string, string | string[]>) => {
+      if (!wsRef.current || wsRef.current.readyState !== WebSocket.OPEN) {
+        onError?.("Not connected");
+        return;
+      }
+
+      // Format answers as display text for user message
+      const answerParts: string[] = [];
+      for (const [, value] of Object.entries(answers)) {
+        if (Array.isArray(value)) {
+          answerParts.push(value.join(", "));
+        } else {
+          answerParts.push(value);
+        }
+      }
+      const displayText = answerParts.join("; ");
+
+      // Add user message to chat
+      setMessages((prev) => [
+        ...prev,
+        {
+          id: generateId(),
+          role: "user",
+          content: displayText,
+          timestamp: new Date(),
+        },
+      ]);
+
+      setCurrentQuestions(null);
+      setIsLoading(true);
+
+      // Send structured answer to server
+      wsRef.current.send(
+        JSON.stringify({
+          type: "answer",
+          answers,
+        }),
+      );
+    },
+    [onError],
+  );
+
   const disconnect = useCallback(() => {
     reconnectAttempts.current = maxReconnectAttempts; // Prevent reconnection
     if (pingIntervalRef.current) {
@@ -350,8 +415,10 @@ export function useAssistantChat({
     isLoading,
     connectionStatus,
     conversationId,
+    currentQuestions,
     start,
     sendMessage,
+    sendAnswer,
     disconnect,
     clearMessages,
   };
diff --git a/ui/src/lib/types.ts b/ui/src/lib/types.ts
index b75d614..ba8eab9 100644
--- a/ui/src/lib/types.ts
+++ b/ui/src/lib/types.ts
@@ -465,6 +465,11 @@ export interface AssistantChatConversationCreatedMessage {
   conversation_id: number
 }
 
+export interface AssistantChatQuestionMessage {
+  type: 'question'
+  questions: SpecQuestion[]
+}
+
 export interface AssistantChatPongMessage {
   type: 'pong'
 }
@@ -472,6 +477,7 @@ export interface AssistantChatPongMessage {
 export type AssistantChatServerMessage =
   | AssistantChatTextMessage
   | AssistantChatToolCallMessage
+  | AssistantChatQuestionMessage
   | AssistantChatResponseDoneMessage
   | AssistantChatErrorMessage
   | AssistantChatConversationCreatedMessage